Acetic Acid → HCID 86690780, compound

HRID 1471742Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[N:9]=[CH:8][C:7]=1[O:14][CH2:15][C:16]1[C:17]([C:22]([NH:24][NH2:25])=O)=[N:18][CH:19]=[CH:20][CH:21]=1.[CH3:26][C:27](O)=O.[CH:30](OC)(OC)OC.[CH:37]([NH2:40])(C)C>O1CCOCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[C:7]([O:14][CH2:15][C:16]2[C:17]([C:22]3[N:24]([CH:27]([CH3:26])[CH3:30])[N:25]=[CH:37][N:40]=3)=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:8][N:9]=[C:10]([O:12][CH3:13])[CH:11]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a mixture of 3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)picolinohydrazide (90 mg, 0.26 mmol, 1 eq.) and AcOH (0.4 mL) in dioxane (2.0 mL) was added CH(OMe)3 (0.4 mL). The mixture was sealed and heated at 110° C. for 1 h, cooled to rt, and added isopropyl amine (0.4 mL). The mixture was re-sealed, heated at 110° C., O/N, concentrated, and purified on RP-HPLC (Gemini 21.2×150 mm) using a mixture of CH3CN and water as eluent to give 4-(1,3-dioxolan-2-yl)-5-((2-(2-isopropyl-2H-1,2,4-triazol-3-yl)pyridin-3-yl)methoxy)-2-methoxypyridine (68 mg, 66%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.66 (dd, J=4.7, 1.2 Hz, 1H), 8.41 (s, 1H), 8.24 (dd, J=8.0, 1.2 Hz, 1H), 7.76 (s, 1H), 7.45 (dd, J=8.0, 4.7 Hz, 1H), 6.90 (s, 1H), 6.17 (s, 1H), 5.61 (s, 2H), 5.30 (sep, J=6.7 Hz, 1H), 4.17-4.02 (m, 4H), 3.88 (s, 3H), 1.55 (d, J=6.7 Hz, 6H). LRMS (M+H+) m/z 398.2.

Workup

customThe mixture was sealed
temperaturecooled to rt
customThe mixture was re-sealed
temperatureheated at 110° C.
concentrationO/N, concentrated
custompurified on RP-HPLC (Gemini 21.2×150 mm)
additiona mixture of CH3CN and water as eluent

Sources & evidence

ORD record: ord-206d1ee1bcc14a6fb5147aff6dfd6de8
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012450B2

Reaction notes

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